“Ava taught him how to sing a torch song. She taught him the hard way.”—Nelson Riddle

The idea is that Frank Sinatra’s impossible, unresolvable romantic relationship with Ava Gardner—for whom he left his wife at a time (1950) when it simply wasn’t done; to whom he was married for a brief, tumultuous period (1951–53*); with whom he tried to reconcile again and again—brought new depths of feeling to his singing, gave him deeper insights into heartache and love. And I would not dispute that reading, if only because the myth of the wound and the bow is too strong to dislodge; if only because Sinatra himself seemed to believe it. And as James Kaplan’s Sinatra: The Chairman makes clear, Frank never really did get over Ava (and vice versa). That torch smoldered as long as she was alive.

But maybe it was more than that. Ava was a sharp woman who knew music: she loved jazz, had been married to bandleader Artie Shaw, and was a fair singer herself (she never forgave MGM for dubbing her voice in Show Boat). What’s more, she had a notoriously acute BS detector and was one of the few people who had the guts to speak truth to Sinatra. No matter how much she loved his talent, she surely would have noticed the increasingly yawning gap between the image of the boyish, puppy-dog-eyed crooner and the reality of the hard-drinking, womanizing, if also oversensitive guy from Jersey who liked to hang out with wise guys. She must have brought this disconnect to his attention, whether as a loving wife trying to help her spouse through a rough patch in his career or as an angry lover lashing out hurtfully. (The latter is somehow more credible; this was the woman who said upon learning of his marriage to Mia Farrow, “I always knew that Frank would end up in bed with a boy.”)

I think it credits both Frank and Ava to see more than heartbreak at work here, but however it came about there’s no denying that Frank Before Ava and After are different animals. After 1953 the callow crooner is gone; the musical intelligence that had once mainly served the beauty of his voice—which he sometimes seemed to treat as a purely physical, almost athletic, gift rather than a means of communication—now served the songs. And he began to approach those songs not as mere material but as autobiography, bringing to them psychological depth, drama, and the ego to persuade us that he had lived them. If Nelson Riddle was right, then every torch song, every love song the mature Frank sang was really about Ava and for Ava—from the joyous celebration of helpless obsession “I’ve Got You Under My Skin” to the bleak but beautiful “Everything Happens to Me.”

The latter is a good test case for Riddle’s theory. Sinatra recorded the Tom Adair–Matt Dennis song three times: He cut it in 1941 with the Tommy Dorsey band when it was brand new, singing it beautifully but really as just another song. His 1956 version was warm, light, philosophical, even hopeful. Sometime in the 1970s Sinatra had Adair write special, personalized lyrics to the song.† It is this version that Sinatra recorded in 1981 as if staring into the void. It was his last great recording, and if it had been included in that year’s She Shot Me Down instead of lesser material (I’m looking at you, Sonny Bono), then that album would have been the classic everyone wanted it to be. It was finally released in 1995 and gave the title to Sinatra’s self-selected 1996 anthology of his “songs of the soul.” It’s a fascinating, revealing choice for the final chapter of the man’s musical autobiography. If this is his final word on things, what did all the success, money, power, and love he accrued mean?

And if Nelson Riddle was right, then this song and all of the songs Frank sang for and about Ava must stand as one of the great romantic monuments.

*The papers weren’t signed until 1957, but the marriage—if not the relationship—was for all intents and purposes over by 1953.

†Sinatra sometimes updated the lyrics to “his” songs, often for comedic effect, often by house scribe Sammy Cahn. This is one of only two cases I am aware of where he went back to the original author of the song to personalize it; the other was, notably, another torch song, Ira Gershwin’s “I Can’t Get Started.”